tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate → tert-butyl N-[(3S)-1-[(1R)-1-[6-[(2E)-2-[(7-ethoxy-6-fluoroquinolin-2-yl)methylidene]hydrazinyl]pyridin-3-yl]-2,2,2-trifluoroethyl]pyrrolidin-3-yl]carbamate

HRID 338947Notes

Reaction equation

HRID 338947 reaction equation
[F:1][C:2]([F:26])([F:25])[C@H:3]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13]1)[C:4]1[CH:5]=[N:6][C:7]([NH:10][NH2:11])=[CH:8][CH:9]=1.[CH2:27]([O:29][C:30]1[CH:39]=[C:38]2[C:33]([CH:34]=[CH:35][C:36]([CH:40]=O)=[N:37]2)=[CH:32][C:31]=1[F:42])[CH3:28]>C(O)C>[CH2:27]([O:29][C:30]1[CH:39]=[C:38]2[C:33]([CH:34]=[CH:35][C:36](/[CH:40]=[N:11]/[NH:10][C:7]3[N:6]=[CH:5][C:4]([C@@H:3]([N:12]4[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:23])[CH3:21])[CH2:13]4)[C:2]([F:25])([F:1])[F:26])=[CH:9][CH:8]=3)=[N:37]2)=[CH:32][C:31]=1[F:42])[CH3:28]

Participants

4

Reactant 2

HCID 86707414tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateHCID 867074687-Ethoxy-6-fluoroquinoline-2-carbaldehyde

Product 1

HCID 140628984tert-butyl N-[(3S)-1-[(1R)-1-[6-[(2E)-2-[(7-ethoxy-6-fluoroquinolin-2-yl)methylidene]hydrazinyl]pyridin-3-yl]-2,2,2-trifluoroethyl]pyrrolidin-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (240 mg, 0.639 mmol) and 7-ethoxy-6-fluoroquinoline-2-carbaldehyde (140 mg, 0.639 mmol) in ethanol (5 mL) were stirred at ambient temperature for 24 hours. After concentration, the residue was used in the next step without purification.

Workup

  1. concentrationAfter concentration
  2. customthe residue was used in the next step without purification

Sources & evidence

ORD record
ord-bb48c85ad0034f028fb97feaae159c36
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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